Webb was most important as a journalist. In 1829 he merged the Courier with Mordecai M. Noah's New York Enquirer. He bought out Noah in 1832, by which time the Courier and Enquirer had the largest daily circulation in the nation, about 4,000. Webb's success was due, in part, to his innovative news-gathering techniques. He maintained a schooner to meet incoming ships before they reached New York, in order to get the foreign newspapers and mail at the earliest moment. He established a special horse express in 1830 and 1831 to bring Jackson's annual messages to New York in advance of the mails, each time beating his rivals by half a day. Webb was one of six founding members of the New York Associated Press in 1848. James Gordon Bennett (1795-1872) of the Herald, Henry J. Raymond of the Times, and James G. Brooks of the Express all learned the newspaper business from Webb, working as associate editors on the Courier and Enquirer.